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The origins of Graham Media can be traced to 1944, when the Washington Post began its broadcasting activities with its purchase of WINX radio in Washington. Four years later the newspaper's parent firm, the Washington Post Company, announced its intention to acquire controlling interest in a rival station, WTOP radio from CBS. The two firms formed a joint venture known as WTOP Incorporated, with the Post holding 55 percent and CBS maintaining the balance (45 percent). The Post sold wholly owned WINX but retained its FM adjunct WINX-FM, which became the original WTOP-FM when the sales became final in 1949. In 1950 WTOP Inc. purchased WOIC, Washington's CBS television affiliate, and changed that station's call letters to WTOP-TV. This Post-CBS joint venture is the direct predecessor of Graham Media Group.

CBS was forced by the Federal Communications Commission to sell its remaining interest in WTOP Inc. in 1954. The Post then merged its Washington stations with recently purchased WMBR-AM-TV in Jacksonville, Florida and changed the company's name to Post Stations, Inc. WMBR radio was later sold off (it is now WQOP); the Post then changed WMBR-TV's calls to WJXT. The company was rechristened as Post-Newsweek Stations, Inc. name after the Post acquired Newsweek magazine in 1961.

In the wake of a panic swap of WTOP-TV (now WUSA) to the (Detroit) Evening News Association for its WWJ-TV (now WDIV) in 1978, followed by the sale of both radio stations later in the year, the Post decided to spin off their broadcasting interests into a company of its own. The Post-Newsweek name itself would later spread to the Post-owned cable operations (now known as Cable One and a company identical in structure to Post-Newsweek Stations).

Post-Newsweek nearly expanded to seven stations in 2008, when it offered to purchase NBC-ownedWTVJ, creating a duopoly with WPLG. The sale was cancelled however, due to lack of FCC approval and poor economic conditions at that time, along with local reaction against media consolidation.[2]

The Post-Newsweek Stations group was not involved in the sales of Newsweek to Sidney Harman in August 2010,[3] and of the Washington Post to Jeff Bezos in October 2013,[4] after which the Washington Post Company was renamed Graham Holdings Company.[5]

In March 2014, Graham Holdings announced that it would sell WPLG to Berkshire Hathaway, in exchange for a large majority of Berkshire Hathaway's shares in Graham Holdings. Berkshire Hathaway and its chairman, Warren Buffett, had been longtime stockholders in the company.[6] The acquisition closed on June 30, 2014; Berkshire Hathaway entered into agreements with Graham to continue providing WPLG with the station group's centralized services for up to two years following the purchase.[7][8][9][10]

Despite being no longer co-owned with either the Washington Post or Newsweek, Graham's station group continued to operate under the Post-Newsweek name until July 28, 2014, when it was announced that it would be renamed Graham Media Group.[11]